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Synlett 2001; 2001(12): 1909-1912
DOI: 10.1055/s-2001-18736
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The Cyclopropylmethylsilane Terminated Prins Reaction: Stereoelectronic Controlled Formation of (E)-Skipped Dienes

D. Christopher Braddock* , D. Michael Badine, Thomas Gottschalk
  • *Department of Chemistry, Imperial College of Science, Technology and Medicine, South Kensington, London, SW7 2AY UK; Fax: + 44(207)5945805; E-mail: c.braddock@ic.ac.uk
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Publication Date:
04 December 2001 (online)

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The reaction of 1-phenyldimethylsilylmethyl-2-vinyl cyclopropane with acetals under the influence of TMSOTf proceeds smoothly to provide skipped dienes with exclusive E-olefin geometry regardless of the initial cis/trans configuration of the starting cyclopropane. The reaction is under stereoelectronic control where the intermediate Prins cation formed is stabilised by the adjacent cyclopropane grouping in a bisected conformation before undergoing silyl-directed collapse.

Prins - skipped dienes - stereoelectronic - cyclopropylmethyl cation - silanes